References
1. The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination|Giovanni Appendino, Nives Daddario, Alberto Minassi, Aniello Schiano Moriello, Luciano De Petrocellis, and Vincenzo Di Marzo, J. Med. Chem., 2005, 48 (14), pp 4663–4669, Publication Date (Web): June 10, 2005 (Article), DOI: 10.1021/jm050139q|Capsaicinoids readily dimerize under biomimetic oxidative conditions,21 and compounds of this type occur naturally in chili pepper. ... Capsaicin is the archetypal obnoxious compound, as testified by its controversial use as an antiriot agent29 and the pungency of chili pepper, its only natural source. ... (b) Bernal, M. A.; Barceló, A. R. 5, 5‘-Dicapsaicin, 4‘-O-5-Dicapsaicin Ether, and Dehydrogenation Polymers with High Molecular Weights are the Main Products of the Oxidation of Capsaicin by Peroxidase from Hot Pepper.||2. Novel Vanilloid Receptor-1 Antagonists: 1. Conformationally Restricted Analogues of trans-Cinnamides|Mark H. Norman, Jiawang Zhu, Christopher Fotsch, Yunxin Bo, Ning Chen, Partha Chakrabarti, Elizabeth M. Doherty, Narender R. Gavva, Nobuko Nishimura, Thomas Nixey, Vassil I. Ognyanov, Robert M. Rzasa, Markian Stec, Sekhar Surapaneni, Rami Tamir, Vellarkad N. Viswanadhan, and James J. S. Treanor, J. Med. Chem., 2007, 50 (15), pp 3497–3514, Publication Date (Web): June 22, 2007 (Article), DOI: 10.1021/jm070189q|This pain target is linked to the natural product capsaicin (1, Figure 1), the pungent component of chili peppers. ... 6 For example, early European folk medicine employed hot pepper extracts (hence capsaicin) to relieve toothaches, and native Americans were also known to have massaged chili pods onto their inflamed gums to ease dental pain. ... (6) Suzuki, T.; Iwai, K. Constituents of Red Pepper Species: Chemistry, Biochemistry, Pharmacology, and Food Science of the Pungent Principle of Capsicum Species.||3. Conformationally Constrained Fatty Acid Ethanolamides as Cannabinoid and Vanilloid Receptor Probes|Giovanni Appendino, Alessia Ligresti, Alberto Minassi, Maria Grazia Cascio, Marco Allarà, Orazio Taglialatela-Scafati, Roger G. Pertwee, Luciano De Petrocellis and Vincenzo Di Marzo, J. Med. Chem., 2009, 52 (9), pp 3001–3009, Publication Date (Web): April 10, 2009 (Article), DOI: 10.1021/jm900130m|The psychotropic agent of hemp (Cannabis sativa L.), and for capsaicin (2a), the pungent principle of chilli pepper (Capsicum annuum L.), sparked intense research activity aimed at evaluating the possibility of developing therapeutic drugs targeting these receptors for a host of pathological conditions that include pain, inflammation, emesis, obesity, neurodegeneration, and cancer. ... VR1 is gated by protons, heat, and the pungent ingredient of hot chili peppers, capsaicin.||4. Discovery of Novel 5,5-Diarylpentadienamides as Orally Available Transient Receptor Potential Vanilloid 1 (TRPV1) Antagonists|Osamu Saku, Hiroshi Ishida, Eri Atsumi, Yoshiyuki Sugimoto, Hiroshi Kodaira, Yoshimitsu Kato, Shiro Shirakura, and Yoshisuke Nakasato,J. Med. Chem., 2012, 55 (7), pp 3436–3451, Publication Date (Web): March 6, 2012 (Article), DOI: 10.1021/jm300101n|The activation of TRPV1 by a diverse range of stimuli including protons, heat, noxious chemicals such as resiniferatoxin(3) and capsaicin,(4) which is the pungent component of hot chili peppers, and endogenous substances such as anandamide(5) and lipoxygenase products(6) leads to an influx of calcium and sodium ions through the channel. ... (11b, 13) Although it was a concern that the dienamide structure would be unstable, piperine (1-piperoylpiperidine), a 5-aryldienamide alkaloid from black pepper and hot peppers, was found to be stable in methanol for several weeks and under different temperature storage conditions.USBio References
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